4-Formylbenzoic acid → HCID 15296710, compound

HRID 1907731Notes

Reaction equation

HRID 1907731 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=O.C(OP([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])(OCC)=O)C.[H-].[Na+].OS([O-])(=O)=O.[K+]>COCCOC.CC(C)=O>[C:24]([O:23][C:21](=[O:22])/[CH:20]=[CH:1]/[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)([CH3:27])([CH3:26])[CH3:25]

Participants

7

Reactant 4

HCID 120884-Formylbenzoic acidHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 2773685tert-Butyl diethylphosphonoacetate

Product 1

HCID 15296710HCID 15296710, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 4-formylbenzoic acid (223) (306 mg, 2.04 mmol) and tert-butyl 2-(diethoxyphosphoryl)acetate (0.8 mL, 3.23 mmol) in ethyleneglycol dimethylether (15 mL) was stirred at 0° C. then treated with sodium hydride (60% in oil, 312 mg, 7.8 mmol), further stirred for 1 h then at room temperature for 3 h. The reaction mixture was diluted with acetone, stirred 10 min then treated with 5% aqueous KHSO4, extracted with DCM. The extract was dried over MgSO4, filtered and concentrated to provide title compound 224 as a white solid (811.5 mg, >100% yield, crude, used in the next step without additional purification).

Workup

  1. waitat room temperature for 3 h
  2. stirringstirred 10 min
  3. extractionextracted with DCM
  4. dry with materialThe extract was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-380d53e60844485ea11437c41f225836
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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